The Roaring Twenties
by King.Enix989
Summary: Year 1922, and Serena and Blair are the most sought after debutant society girls in Manhattan. Serena longs for the life of a flapper, and Blair longs for something she surely shouldn't, a Chuck Bass, bootlegger, and gangster. What will we do with them?
1. Society Girl's Don't Smoke Cigars

Serena van der Woodsen was not a good girl. She liked boys, and boys liked her. The year was 1922 and the debutante ball was the last place she felt like being. She was wearing a dark blue silk dress, and her hair was done up intricately, though she fantasized about raunchy nightclubs and sweaty faced boys slapping her butt.

"Can I have this dance?" Nate Archibald, the golden boy, asked Serena. In all respects, Nate was perfect for Serena. He was just has handsome as she was beautiful, he was just as wealthy as she was rich, and he was just as charming as she was graceful. The issue was that Serena didn't like rich, charming, nice boys, Serena wanted a rough, greasy-

"You look beautiful in that dress." Nate whispered, holding her waist a little too sexually.

Although the society pages dubbed Serena as pure as a lily petal, Serena and Nate had had beautiful passionate sex together countless times. Everything was about appearances. They appeared to twirl around the dance floor like the innocent, privileged youth everyone knew them to be. But actually, Nate gripped Serena's waist imagining her naked on his white linen sheets, and Serena was hot for Nate's touch.

"Look at you two lovebirds!" Blair twirled by in the arms of some handsome and wealthy possible husband. Blair Waldorf was actual a virginal flower. Though she was Serena's truest and dearest friend, they were polar opposites. Blair enjoyed the finer things, the expensive, and the high-class. If Serena ever brought up her sick fantasies about factory workers and farm-boys Blair instantly tuned out.

Behind Serena, Blair was the society girl everyone wanted to be. Serena's money was slightly older, and slightly larger. Serena was slightly more charming, and more fun. Blair was what you might call, a bitch? Nevertheless, Serena saw something in her best friend that others missed.

"Nate, get me the hell out of here." Serena whispered. Nate grew excited, but Serena soon crushed that, "I want to go to a bar!"

"But doll, you know that's illegal!" Nate smiled brightly, his family recently moved from Georgia to New York. Nate had confided to Serena that his father was a part of bootlegging alcohol. As Nate and Serena gracefully made their exit, Serena snatched Blair along.

The Back Room, a New York Speakeasy was soo beneath Blair that she almost cried when Serena dragged her in. She knew for certain that they would be robbed by the common drunkard. She was wearing fucking diamonds! "SERENA!" Blair hissed, "Aren't you a bit concerned about your valuables" Blair was talking about more than jewelry.

"Stick it wear you will NEVER let any boy enter!" Serena said giggling as she dragged Blair through the door. Nate led the girls through the cheering, drunken men. A girl was on stage singing. Serena felt at home. She jumped with joy when some young kid, too young to be in an illegal bar, pinched her butt.

Blair held back the tears, her eyes were already watering mainly from the musty smell of these unwashed lower-class fools. She was almost crying because if the police did a bust she would get arrested and put in jail with these unwashed, lower class fools. And heaven forbid anyone who was anyone see her anywhere near this place, or it would drown the society column with her shame.

Nate led them to somesort of backroom. Three men were playing cards, the cigar smoke almost killed Blair on impact. Serena inhaled the smoke, because it gave her a mini orgasm in her nose. The men had women drapped over them, encouraging them to bet higher. Blair would be damned if that's what Nate brought her in here to do.

"CHUCK BASS YOU DOG!" Nate called. A dark haired man smiled when Nate entered, "ARCHIBALD! Pull up a chair!"

Serena whispered in Blair's ear, "That is Chuck Bass, his father is the biggest bootlegger in the country, and apparently like directly linked with mob bosses. He is so rich from everything illegal it's like…fantastic." Serena said.

"Who are these classy ladies?"

"Serena!" Serena chimed, obviously enticed by Chuck's debonair way of talking with a cigar.

Blair hated to look feeble, especially next to Serena, "Blair." She said in a deep sexy voice, resisting the cough that aided her in the deep sexy voice.

"Blair?" He echoed, and winked at her.

"Stop flirting and put your cards down Bass!" Nate said, joining the poker game. Blair couldn't take her eyes off of Chuck's, he was looking at her like no one had before. "Serena we need to go!" she said grabbing Serena's dainty wrist.

"Blaaaaaaaair." Serena droned.

"Stay sweetie, I'll take her home." Chuck said.

"No! No thank you! NO! Sit back down please! Stop!" Blair said as Chuck made his way towards her, cigar in lips. Serena and Nate giggled at Blair's girlish squeal. Serena took a swig of someone's beer and started to kiss Nate's neck, forgetting all about her friend.

"The lady doth protest too much!" Chuck said looking Blair up and down.

"The lady dothent!" She cried, "And don't look at me you dog!"

"IT wouldn't be very gentlemanly of me to let you go home alone sweetheart." He whispered close to her face, smoke trailing out of his lips like water.

Blair turned around and stormed out, pretending to ignore Chuck following her. She hated bars, and alcohol, and smoke, and cards, and men who sold alcohol, and Serena, and Nate, and Chuck, and-

She found herself standing in the rain. She began to sob. "Let me give you a lift." Chuck said from behind her. "I have a car." He teased. Blair realized she was ruining her green chiffon dress, not that she would ever wear it again but the principle!

"OKAY!" She screamed, stamping her foot in a puddle.


	2. Horse Races and Red Faces

Serena became bored of Nate playing cards and snuck out of the little room. She cruised the bar for a guy to talk to. The one who had pinched her earlier was still there, taking her clothes off with his eyes. She made her way over to him. "Hi, I'm Serena." She shouted over the voices of drunken poor people.

"Oliver!" he shouted back. Oliver hadn't shaven in a few days, or bathed. He was wearing a shirt with grease all over it so Serena assumed he worked in a factory. He was really young and ruggedly handsome however. Serena was not sure what to do, now, she almost asked him could she sit down but he pulled her down onto his lap without permission.

Laughing he said, "So that's a purty dress you got on ma'am!" he said.

"Thank you! I stole it!" She said giggling.

"You're brave! I like that in a woman." He said feeling her up. Serena could feel his excitement growing under her.

Nate walked up, "Serena, I think it's time we go." He said, with an angry and confused look on his face. Serena looked at him, and heard his words, but they didn't process in her head.

"Alright, bye." She said turning around to kiss Oliver. Nate pulled Serena off of Oliver, who stood up angrily. Nate sort of slung Serena to the side before he took a punch to the jaw from Oliver. Nate had never been hit in his life before and he certainly wasn't going to ruin his face fighting. That single punch started an uproar anyone that Nate used to drag Serena safely out of the bar.

Blair was not having quite as much fun. Blair sat as far as she could from Chuck Bass in his car. She had no idea how she would sneak into her house looking like this. She couldn't go home.

"I can't go home." She said. "Take me to your house." She pleaded.

"Surely." Chuck said with a dirty smirk.

"No, so I can freshen up and walk into my house as if I never went to that disgusting speakeasy!" Blair shrieked.

Chuck laughed at her.

"I hope you don't think we are equals." Blair said pouting.

"Hm?"

"I have class and you don't. My money is from honest business, yours is from crime. You are never to speak as though you have met me." Blair said strictly.

"Yes, your majesty." Chuck giggled more.

"Do you know who I am?"

"Blair Waldorf. Super Manhattan society girl whose father owns the largest law firm in the country, as well as various restaurants. Now sweetie, do you know who I am?" He said, turning his sharp gaze toward her. She jumped and looked away when she realized she was a bunny caught by a snake.

"Chuck Bass. My father talks about yours. How he has dealt with cases dealing with the notorious Bart Bass, but how they couldn't stick him. Also I know that your father is a bootlegger and works directly with the Italian mafia!" Blair said accusingly.

"Bravo!" Chuck said clapping. He edged closer to Blair, offering her champagne.

"No thank you! I don't drink, if you hadn't heard, it's actually illegal." She said. Chuck kissed her neck, she didn't want him to stop but she made him. She pushed his head away and pretended nothing had happened until they got to his mansion.

Chuck had his maids clean Blair and her dress up, and then sent her home alone.

Nate and Serena went to a horse race the next morning as if nothing had happened. They had been parading as young lovers for a year now, and Serena was worried that Nate was getting serious.

Serena was wearing a white sundress, and giant hat adorned with doves and lilies. Nate's jockey friend approached them. Of course he started to flirt with her, and everything Serena did could be perceived as flirtatious, but she wasn't really paying attention to him. Serena was watching the horse-hand behind the Jockey. He had hard brown curls and muscles that spoke "I have been working all my life lifting hay and training horses."

"Tony, how about we come over to your house in the Hamptons for dinner! I'd love to see your horses." Serena said, touching Tony's slip arm. When Serena did that, she would be damned if a boy refused her.

"Sure! I live in Tennessee so I don't know many people out here in New York so invite whoever!"

Later that night, Serena wearing a red dress dragged Blair in black to Tony's Hamptons house. Nate tagged along (they actually didn't have any other friends because they were so stuck up and didn't want to admit it).

Blair walked in the door expecting to be bored out of her mind as Serena found clever ways to meet the stable hand boy, at the same time as flirting viciously with Nate and Tony. To Blair's dismay, sitting at the table on the patio that overlooked Tony's fields was Chuck Bass. She felt in her unworked bones that Serena was going to jump up and say "CHUCK!" so Blair beat her to it.

"How do you do? I'm Blair Waldorf." First to Tony and then to Chuck who didn't even stand like a gentlemen, just sat there smirking in his seat. Blair hoped to God that Serena got the hint that they were supposed to never have met Chuck Bass.

"I'm Serena van der Woodsen." She said coyly. "TONY! I am dying to meet all of your horses! Do they have names! Oh can we go now before it gets dark?"

"I guess, if you really want to." Tony was so small and weak. His parents didn't want him being a jockey but they couldn't stop him. His father was a famous horse trader and breeder.

Serena and Blair walked arm in arm, following the boys who strolled along toward the stable.

"I wonder how Tony knows Chuck. I bet Chuck illegally bets on Tony's horses." Blair said. Serena was not listening.

"That stable hand was so…masculine. He smiled at me." Serena gushed into Blair's cynical ear.

"All boys smile at you Serena." Blair said rolling her eyes. Chuck looked back and winked at her, and she looked away blushing into the autumn breeze.

**A/N: Will Serena meet the stable hand boy? Will Chuck try something with Blair again tonight? You won't know until next Friday so ALERT and SUBSCRIBE and FAVORITE and REVIEW PLEASSE!**


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